JP4173191B2 - Ｈ３リガンドとして有用な３‐または４‐一置換フェノールおよびチオフェノール誘導体 - Google Patents

Ｈ３リガンドとして有用な３‐または４‐一置換フェノールおよびチオフェノール誘導体 Download PDF

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JP4173191B2
JP4173191B2 JP2007512541A JP2007512541A JP4173191B2 JP 4173191 B2 JP4173191 B2 JP 4173191B2 JP 2007512541 A JP2007512541 A JP 2007512541A JP 2007512541 A JP2007512541 A JP 2007512541A JP 4173191 B2 JP4173191 B2 JP 4173191B2
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phenyl
pyran
tetrahydro
pyrrolidin
methyl
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JP2007536365A (ja
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ベルナードゥリ，パトリック
マイケル クローニン，アンドリュー
デニ，アレクシ
マーティン デントン，スティーブン
ジャコベリ，アンリ
イアン ケンプ，マーク
ローティオワ，エドウィージュ
ルソー，フィオナ
セラデル−シビ，デルフィーヌ
ベルヌ，ファブリス
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ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー
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Priority claimed from GB0504564A external-priority patent/GB0504564D0/en
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Families Citing this family (25)

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MY150088A (en) 2003-05-19 2013-11-29 Irm Llc Immunosuppressant compounds and compositions
JP2007517056A (ja) 2003-12-29 2007-06-28 セプラコア インコーポレーテッド ピロール及びピラゾールｄａａｏ阻害剤
JP2006213674A (ja) * 2005-02-07 2006-08-17 Ube Ind Ltd ４−ホルミルテトラヒドロピラン化合物の製法
JP2009500425A (ja) 2005-07-06 2009-01-08 セプラコア インコーポレーテッド エスゾピクロン及びトランス４−（３，４−ジクロロフェニル）−１，２，３，４−テトラヒドロ−ｎ−メチル−１−ナフタレンアミン又はトランス４−（３，４−ジクロロフェニル）−１，２，３，４−テトラヒドロ−１−ナフタレンアミンの組み合わせ、並びに閉経期並びに気分、不安、及び認知障害の治療方法
WO2007045989A1 (en) * 2005-10-20 2007-04-26 Pfizer Limited Pyridyl derivatives useful as h3 ligands
RU2430913C2 (ru) 2006-01-06 2011-10-10 Сепракор Инк. Циклоалкиламины в качестве ингибиторов повторного поглощения моноамина
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DK2013835T3 (en) 2006-03-31 2015-12-14 Sunovion Pharmaceuticals Inc Preparation of chiral amides and AMINES
MX2008013137A (es) 2006-04-11 2008-10-21 Novartis Ag Compuestos organicos.
EP2049472B1 (en) * 2006-06-23 2015-01-21 AbbVie Bahamas Ltd. Cyclopropyl amine derivatives as histamin h3 receptor modulators
US9108948B2 (en) * 2006-06-23 2015-08-18 Abbvie Inc. Cyclopropyl amine derivatives
US7884124B2 (en) 2006-06-30 2011-02-08 Sepracor Inc. Fluoro-substituted inhibitors of D-amino acid oxidase
WO2008077597A1 (en) * 2006-12-22 2008-07-03 Novartis Ag 1-aminomethyl- l- phenyl- cyclohexane derivatives as ddp-iv inhibitors
US7902252B2 (en) 2007-01-18 2011-03-08 Sepracor, Inc. Inhibitors of D-amino acid oxidase
MX2009012685A (es) 2007-05-31 2009-12-14 Sepracor Inc Cicloalquilaminas sustituidas con fenilo como inhibidores de la reabsorcion de monoamina.
TW201039822A (en) 2009-02-06 2010-11-16 Taisho Pharmaceutical Co Ltd Dihydroquinolinone derivatives
US9186353B2 (en) 2009-04-27 2015-11-17 Abbvie Inc. Treatment of osteoarthritis pain
SG186885A1 (en) 2010-06-04 2013-02-28 Albany Molecular Res Inc Glycine transporter-1 inhibitors, methods of making them, and uses thereof
US8853390B2 (en) 2010-09-16 2014-10-07 Abbvie Inc. Processes for preparing 1,2-substituted cyclopropyl derivatives
CN103906746B (zh) * 2011-10-26 2015-12-09 辉瑞有限公司 用作钠通道调节剂的(4-苯基咪唑-2-基)乙胺衍生物
WO2014095534A1 (en) * 2012-12-19 2014-06-26 Basf Se New substituted triazoles and imidazoles and their use as fungicides
ES2647965T3 (es) * 2013-01-09 2017-12-27 Arena Pharmaceuticals, Inc. Derivados de bifenil-etil-pirrolidina como moduladores del receptor de histamina H3 para el tratamiento de trastornos cognitivos
TWI731317B (zh) * 2013-12-10 2021-06-21 美商健臻公司 原肌球蛋白相關之激酶（ｔｒｋ）抑制劑
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CN113336715B (zh) * 2021-08-04 2021-11-23 山东海利尔化工有限公司 一种含二氧戊环的三唑类化合物及其中间体的制备方法

Family Cites Families (5)

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Publication number Priority date Publication date Assignee Title
DE3024836A1 (de) * 1980-07-01 1982-01-28 A. Nattermann & Cie GmbH, 5000 Köln (3-alkylamino-2-hydroxy-propoxy)-benzylnitrile, verfahren zu deren herstellung und diese als wirkstof enthaltende arzneimittel
DK368687A (da) * 1986-11-21 1988-05-22 Cheminova As Aminoalkylerede hydroxyforbindelser og deres anvendelse som fungicider
JP4516717B2 (ja) * 2000-07-13 2010-08-04 アボット・ラボラトリーズ ヒスタミン−３受容体リガンドとしての１，３−二置換ピロリジン及び１，３，３−三置換ピロリジン並びにそれらの治療的応用
DK1311482T3 (da) * 2000-08-08 2007-05-07 Ortho Mcneil Pharm Inc Ikke-imidazolaryloxypiperidiner som H3-receptorligander
EP1379493A2 (en) * 2001-03-23 2004-01-14 Eli Lilly and Company Non-imidazole aryl alkylamines compounds as histamine h3 receptor antagonists, preparation and therapeutic uses

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